2,4-Imidazolidinediones, compositions and herbicidal method

Abstract

5-(Dialkylamino)methylene-1,3-disubstituted-2,4-imidazolidinediones are useful herbicidal agents.

I claim: 
     
       1. A compound of the formula: ##STR3## wherein: R 1  and R 2  independently are lower alkyl, phenyl, or phenyl substituted with one or two groups selected from halo, lower alkyl, halo lower alkyl, lower alkoxy or nitro, and R 3  and R 4  independently are methyl or ethyl. 
     
     
       2. The compound of claim 1 wherein R 1  is lower alkyl and R 3  and R 4  both are methyl. 
     
     
       3. The compound of claim 2 wherein R 2  is phenyl or mono- or di-substituted phenyl. 
     
     
       4. The compound of claim 3, said compound being 5-(dimethylamino)methylene-3-methyl-1-(3-trifluoromethylphenyl)-2,4-imidazolidinedione. 
     
     
       5. The compound of claim 1 wherein R 2  is lower alkyl and R 3  and R 4  both are methyl. 
     
     
       6. The compound of claim 5 wherein R 1  is phenyl or mono- or disubstituted phenyl. 
     
     
       7. The compound of claim 6 wherein R 2  is methyl. 
     
     
       8. The compound of claim 7 wherein R 1  is phenyl. 
     
     
       9. The compound of claim 7 wherein R 1  is chlorophenyl, dichlorophenyl, methylphenyl, methoxyphenyl, nitrophenyl or trifluoromethylphenyl. 
     
     
       10. The compound of claim 9 wherein R 1  is 2-chlorophenyl. 
     
     
       11. The compound of claim 9 wherein R 1  is 3-chlorophenyl. 
     
     
       12. The compound of claim 9 wherein R 1  is 4-chlorophenyl. 
     
     
       13. The compound of claim 9 wherein R 1  is 3-methylphenyl. 
     
     
       14. The compound of claim 9 wherein R 1  is 4-methylphenyl. 
     
     
       15. The compound of claim 9 wherein R 1  is 3-nitrophenyl. 
     
     
       16. The compound of claim 9 wherein R 1  is 4-methoxyphenyl. 
     
     
       17. The compound of claim 9 wherein R 1  is 3-trifluoromethylphenyl. 
     
     
       18. The compound of claim 9 wherein R 1  is 3,4-dichlorophenyl. 
     
     
       19. A herbicidal method for controlling undesired plant growth comprising applying to said undesired plants or the the soil where vegetative control is desired a herbicidally effective amount of a compound of claim 1. 
     
     
       20. The method of claim 19 employing a compound wherein R 1  is lower alkyl, R 2  is phenyl, mono- or disubstituted phenyl and R 3  and R 4  both are methyl. 
     
     
       21. The method of claim 19 employing a compound wherein R 1  is phenyl, mono- or disubstituted phenyl R 2  is lower alkyl and R 3  and R 4  both are methyl. 
     
     
       22. The method of claim 21 employing a compound wherein R 2  is methyl. 
     
     
       23. The method of claim 22 employing a compound wherein R 1  is phenyl, chlorophenyl, dichlorophenyl, methylphenyl, methoxyphenyl, nitrophenyl, or trifluoromethylphenyl. 
     
     
       24. The method of claim 23 employing a compound wherein R 1  is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-methylphenyl, 4-methylphenyl, 3-nitrophenyl, 4-methoxyphenyl or 3-trifluoromethylphenyl. 
     
     
       25. A herbicidal composition comprising from about 0.1 to about 95.0 percent by weight of a compound of claim 1 admixed with a suitable agricultural carrier. 
     
     
       26. The composition of claim 25 employing a compound wherein R 1  is lower alkyl, R 2  is phenyl, mono- or disubstituted phenyl, and R 3  and R 4  both are methyl. 
     
     
       27. The composition of claim 26 employing a compound wherein R 1  is methyl and R 2  is 3-trifluoromethylphenyl. 
     
     
       28. The composition of claim 25 employing a compound wherein R 1  is phenyl, or mono- or disubstituted phenyl, R 2  is lower alkyl, and R 3  and R 4  both are methyl. 
     
     
       29. The composition of claim 28 employing a compound wherein R 2  is methyl. 
     
     
       30. The composition of claim 30 employing a compound wherein R 1  is phenyl, chlorophenyl, dichlorophenyl, methylphenyl, methoxyphenyl, nitrophenyl, or trifluoromethylphenyl. 
     
     
       31. The composition of claim 30 employing a compound wherein R 1  is 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-methylphenyl, 4-methylphenyl, 3-nitrophenyl, 4-methoxyphenyl or 3-trifluoromethylphenyl.